Reaction #494367

Reaction equation

D-glucose

B-NADP

MeCN

Potassium chloride

acetonitrile

→

(3S)-4,4-dimethoxytetrahydro-2H-pyran-3-ol

Solvents

toluene

Conditions

Workup

1. 1
   ExtractionThe above organic solution of 4,4-dimethoxydihydro-2H-pyran-3(4H)-one was extracted 3× with phosphate
2. 2
   Otherexceeded 27° C.
3. 3
   workup.ADDITIONKRED-130 (1.60 g, 499 mmol) were added
4. 4
   workup.WAITAfter 30 min
5. 5
   Otherthe reaction mixture was transferred to 6 L sep funnel
6. 6
   ExtractionThe aqueous layer was back extracted 1×
7. 7
   workup.ADDITIONwith a mixture of acetonitrile (1.95 L) and toluene (0.65 L), and 1× with acetonitrile (1.5 L)
8. 8
   ConcentrationThe combined organic extracts were concentrated in vacuo

Procedure

The above organic solution of 4,4-dimethoxydihydro-2H-pyran-3(4H)-one was extracted 3× with phosphate buffered water (0.55 L). To the combined aqueous extracts was added D-glucose (180 g, 100 mmol), and the solution was heated to 30° C. When the solution exceeded 27° C. upon heating B-NADP+ (1.60 g, 499 mmol) GDH-103 (1.60 g, 499 mmol) and KRED-130 (1.60 g, 499 mmol) were added and the mixture was stirred for 17 h at 30° C. Potassium chloride (200 g, 2.68 mol) and acetonitrile (1.3 L) were added. After 30 min, the reaction mixture was transferred to 6 L sep funnel and additional MeCN (0.67 L) and toluene (0.87 L) were added. The aqueous layer was back extracted 1× with a mixture of acetonitrile (1.95 L) and toluene (0.65 L), and 1× with acetonitrile (1.5 L). The combined organic extracts were concentrated in vacuo to provide (3S)-4,4-dimethoxytetrahydro-2H-pyran-3-ol.

Source